Radiation curable (meth)acrylated compounds may be produced commercially from petrochemical sources. The world's supply of petroleum is being depleted and eventually the demand for petrochemical derived products may outstrip the available supply. As a consequence, the market price of petroleum and petroleum derived products would increase making them less desirable.
Biology offers an attractive alternative for industrial manufacturers looking to reduce or replace their reliance on petroleum and petrochemical derived products. The replacement of petrochemicals and petrochemical derived products with products or feedstock derived from biological resources (bioderived products) may offer many advantages. Products and feedstock from biological sources are renewable, it may also be a response to the increasing demand for environmentally friendly products and to the price increase of petrochemical derived products.
Bioderived cyclic ether polyols obtained from various crops present a unique chemical structure that could fulfill the need for safer and more sustainable radiation curable resins. The non-aromatic cyclic structure of these derivatives provides high tensile modulus and high glass transition temperature.
The preparation of cyclic ester polyols from biological feedstock such as corn, wheat or cellulose is known and some acrylates made from these have already been described in several publications.
However, the known acrylate derivatives of bioderived cyclic ester polyols are limited to the direct acrylation of the polyols or of their alkoxylated derivatives.
US 2009/0018300 discloses several bioderived polyols and their acrylate derivatives, which are used as building blocks for the synthesis of polymers.
WO 2011/048739 and WO 2011/048750 disclose the acrylate derivative of isosorbide and radiation curable compositions thereof. These products and compositions show unexpected high cure speeds combined with low viscosities and acceptable ink or coating properties.
Few other acrylate derivatives of cyclic ether polyols are described in the art. WO 2009/153168, WO 2007/120459 and US 2002/0013482 describe aromatic (meth)acrylated derivatives of cyclic ether polyols and their use as chiral compounds.
On the other hand, there is today a real market need for the development of a broad range of bioderived radiation curable (meth)acrylated compounds for use in radiation curable compositions for the coatings, inks, overprint varnishes, adhesives and composites.